Water → 5-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine

HRID 324392

Reaction equation

HRID 324392 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[Br:7][C:8]1[C:9](Cl)=[N:10][C:11](Cl)=[N:12][CH:13]=1.[OH2:16]>O1CCCC1>[Br:7][C:8]1[C:9]([O:16][C:2]([CH3:5])([CH3:3])[CH3:1])=[N:10][C:11]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 8188515-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium tert-butoxide (67.5 g) in tetrahydrofuran (500 ml) was added 5-bromo-2,4-dichloropyrimidine (55 g) (J. Am. Chem. Soc., 1934, 56, 134) in tetrahydrofuran (100 ml) dropwise. After 1.5 hours water (100 ml) was added carefully and the mixture extracted with ethyl acetate. The combined organic solution was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with isohexane containing 1% triethylamine.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined organic solution was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with isohexane containing 1% triethylamine

Sources & evidence

ORD record
ord-2fa5f3caf1ce486d911a5439d93c7e09
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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